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Chemical Structure| 1319738-37-8 Chemical Structure| 1319738-37-8

Structure of 1319738-37-8

Chemical Structure| 1319738-37-8

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Product Details of [ 1319738-37-8 ]

CAS No. :1319738-37-8
Formula : C15H21NO3
M.W : 263.33
SMILES Code : O=C1N([C@H](C2=CC=C(OC)C=C2)C)C[C@H]([C@@H](O)C)C1

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Application In Synthesis of [ 1319738-37-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1319738-37-8 ]

[ 1319738-37-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1319738-37-8 ]
  • [ 1261677-80-8 ]
  • C24H25BrN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃; A Example 27100 mg of 7-Bromo-quinolin-5-ol, 234 mg triphenylphosphine and 133 mg of (R)-4-((S)-l- hydroxyethyl)-l-((S)-l-(4-methoxyphenyl)ethyl)pyrrolidin-2-one was dissolved in 2.5 mL of DCM and 7.5 mL of THF. 205 mg DBAD was added (slightly exothermic) and the mixture was stirred overnight at room temperature. Then additional 234 mg triphenylphosphine and 205 mg DBAD was added and the mixture stirred over the weekend. The mixture was diluted with DCM and extracted with IN NaOH and water and the organic phase was concentrated in vacuo. The remaining material was treated with 2 mL of trifluoracetic acid (TFA) and heated 2 h and 15 min at 90C in the microwave. The mixture was concentrated and purified with HPLC (XbridgeC18, MeOH / water, TFA) to yield 165 mg yellow solid which was purified by FCC over silica ( 20 g Si02; DCM^ DCM: MeOH 90: 10) to yield 90 mg solid as Example 27. Analysis: HPLC-MS: Rt = 0.56 min (method X001 002), M+H = 335/337. 1H-NMR (400 MHz, DMSO-d6): delta = 8.95 (lH,d), 8.50 (lH,d), 7.80 (lH,s), 7.57 (2H, m), 7.30 (1H, s), 4.85 (1H, m), 3.40 (1H, t), 3.15-3.10 (1H, m), 2.82 (1H, m), 2.40-2.22 (2H,m), 1.32 (3H,d) ppm.
  • 2
  • [ 1319738-37-8 ]
  • [ 1261677-80-8 ]
  • [ 1421339-96-9 ]
YieldReaction ConditionsOperation in experiment
90 mg Synthesis of (R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one (Example 27) 100 mg of 7-Bromo-quinolin-5-ol, 234 mg triphenylphosphine and 133 mg of (R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one was dissolved in 2.5 mL of DCM and 7.5 mL of THF. 205 mg DBAD was added (slightly exothermic) and the mixture was stirred overnight at room temperature. Then additional 234 mg triphenylphosphine and 205 mg DBAD was added and the mixture stirred over the weekend. The mixture was diluted with DCM and extracted with 1N NaOH and water and the organic phase was concentrated in vacuo. The remaining material was treated with 2 mL of trifluoracetic acid (TFA) and heated 2 h and 15 min at 90 C. in the microwave. The mixture was concentrated and purified with HPLC (XbridgeC18, MeOH/water, TFA) to yield 165 mg yellow solid which was purified by FCC over silica (20 g SiO2; DCM?DCM:MeOH 90:10) to yield 90 mg solid as Example 27. Analysis: HPLC-MS: Rt=0.56 min (method X001-002), M+H=335/337. 1H-NMR (400 MHz, DMSO-d6): delta=8.95 (1H, d), 8.50 (1H, d), 7.80 (1H, s), 7.57 (2H, m), 7.30 (1H, s), 4.85 (1H, m), 3.40 (1H, t), 3.15-3.10 (1H, m), 2.82 (1H, m), 2.40-2.22 (2H, m), 1.32 (3H, d) ppm.
 

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